4-Aminopyridine → HCID 178469618, compound

HRID 842030Notes

Reaction equation

HRID 842030 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C([O:10][CH:11]=[C:12]([C:18](OCC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])C>>[CH2:16]([O:15][C:13]([C:12]1[CH:18]=[N:1][C:2]2[C:7]([C:11]=1[OH:10])=[CH:6][N:5]=[CH:4][CH:3]=2)=[O:14])[CH3:17]

Participants

3

Reactant 2

HCID 17274-AminopyridineHCID 6871Diethyl (ethoxymethylene)malonate

Product 1

HCID 178469618HCID 178469618, compound

Procedure

4-Aminopyridine (15.84 g) and diethyl ethoxymethylenemalonate (34.3 ml) were heated at 110° C. then allowed to stand for 16 h at room temperture. The resulting solid was collected by filtration, washed wtih diethyl ether then pentane and dried in vacuo. A sample of the resulting enamine (10.0 g) was added portionwise to refluxing Dowtherm A (400 ml ). After heating for a further 0.25 h the reaction mixture was cooled then diluted with pentane (400 ml). The precipitated solid was collected by filtration and washed wtih diethyl ether to afford the title compound as a beige solide (3.84 g).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed wtih diethyl ether
  3. dry with materialpentane and dried in vacuo
  4. additionA sample of the resulting enamine (10.0 g) was added portionwise
  5. temperatureto refluxing Dowtherm A (400 ml )
  6. temperatureAfter heating for a further 0.25 h the reaction mixture
  7. temperaturewas cooled
  8. additionthen diluted with pentane (400 ml)
  9. filtrationThe precipitated solid was collected by filtration
  10. washwashed wtih diethyl ether

Sources & evidence

ORD record
ord-a7a5decec57540fa9b9427075b137500
Source dataset
uspto-grants-2002_04
Patent number
US06372757B1

Reaction notes

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